- An improved method for the synthesis of γ-DDB
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A mild and efficient method for the synthesis γ-DDB has been developed through anhydride-linker assisted intramolecular Ullmann reaction. Highly regioselective bromination of differentially protected gallate was realized by virtue of the introduction of NBS.
- Song, Chuanjun,Zhao, Peng,Hu, Zhiqiang,Shi, Shuai,Cui, Yanmei,Chang, Junbiao
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- Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core
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A stereoselective synthesis of the dibenzocyclooctadiene lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki-Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey-Bakshi-Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.
- Venkanna, Arramshetti,Poornima, Borra,Siva, Bandi,Babu, B. Hari,Babu, K. Suresh
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- Asymmetrie synthesis of (+)- and (-)-wuweizisu C stereoisomers and their chemosensitizing effects on multidrug-resistant cancer cells
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Total syntheses of the dibenzocyclooctadiene natural product wuweizisu C in its (-)-form [(S)-1] and its (+)-form [(R)-l] were achieved in 19 steps, starting from commercially available gallic acid. In the key step, the asymmetric biphenyl axis was constructed by an oxazoline-mediated Ullmann reaction to provide either the P or Mbiaryl product in 68% yield and >99% de, depending on the configuration of the oxazoline. The efficiency of this total synthesis was excellent, as the syntheses of (S)-1 and (R)-1 from, intermediate 7 each proceeded in 13 steps with an overall yield of 6.8%. (S)-1 and (R)-1 were evaluated as chemosensitizers for multidrug-resistant cancers.
- Li, Yanfeng,Wang, Qiang,Dong, Lihong,Guo, Xiaohe,Wang, Wei,Xie, Jingxi,Chang, Junbiao
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- Rhodium-Catalyzed Twofold Unsymmetrical C-H Alkenylation-Annulation/Thiolation Reaction to Access Thiobenzofurans
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A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed, enabling the straightforward and efficient synthesis of various thiobenzofurans in one step. This robust protocol proceeds with a broad substrate scope and good functional group tolerance under relatively mild reaction conditions.
- Lin, Jian,Hu, Liuyu,Chen, Chao,Feng, Huijin,Yu, Yang,Yang, Yaxi,Zhou, Bing
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supporting information
p. 1194 - 1198
(2021/02/20)
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- Nitrogen-containing biaromatic ring compounds as well as preparation method and application thereof
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The invention relates to nitrogen-containing biaromatic ring compounds, a preparation method and an application, namely a pharmaceutical composition consisting of the compound as an effective component, a preparation method and an application of the compound in resisting liver cancer. A series of nitrogen-containing biaromatic ring compounds with novel structures are synthesized, generation of miRNA is induced by regulating TRBP, a good anti-liver cancer effect is shown, small molecules have a relatively strong inhibiting effect on proliferation of liver cancer cells, individual compounds even have a better curative effect than enoxacin, no similar structure has the effect before, and the compounds have good development prospects.
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Paragraph 0046; 0054
(2021/07/11)
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- Nitrogen-Containing Biphenyl Compounds, Pharmaceutical Compositions of Same, Preparation Methods and Anti-HIV-1 Uses Thereof
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Nitrogen-containing biphenyl compounds as represented by formula (I), pharmaceutically acceptable salts or derivatives thereof, pharmaceutical compositions, and preparation methods therefore, and anti-HIV-1 use of the compound. Each substituent group in formula (I) is as defined in the description.
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- ANALGESIC THAT BINDS FILAMIN A
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A compound, composition and method are disclosed that can provide analgesia. A contemplated compound has a structure that corresponds to Formula A, wherein A, B, X, R1, R2, R7 and R8, and the dashed lines are defined within.
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Page/Page column 124
(2010/05/14)
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- The first total synthesis of neohelmanticins A-D, amino derivatives of the 1,2-dihydroxypropane core and biological evaluation
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A concise total synthesis of neohelmanticins A-D has been accomplished in 15 steps starting from commercially available gallic acid. Swern oxidation conditions, a Grignard reaction, Sharpless kinetic resolution, and regioselective ring opening of an epoxide with lithium aluminum hydride (LAH) are the key features to install the basic core, dihydroxy phenyl propane 2. One hydroxyl group of this core was esterified with tiglic acid followed by the oxidation and esterification with corresponding acids to yield neohelmanticins A-D.
- Sreedhar, Eppakayala,Sateesh Chandra Kumar,Venkateswar Reddy,Robinson,Suresh Babu,Madhusudana Rao,Srinivas
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experimental part
p. 440 - 448
(2009/09/06)
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- Synthesis of unsymmetrical biphenyls as potent cytotoxic agents
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Twenty-six unsymmetrical biphenyls were synthesized and evaluated for cytotoxic activity against DU145, A549, KB and KB-Vin tumor cell lines. Three compounds 27, 35 and 40 showed very potent activity against the HTCL panel with an IC50 value range of 0.04-3.23 μM. In addition, fourteen active compounds were all more potent against the drug-resistant KB-Vin cell line than the parental KB cell line. Preliminary SAR analysis indicated that two bulky substituents on the 2,2′-positions of unsymmetrical biphenyl skeleton are necessary and crucial for in vitro anticancer activity, thus providing a good starting point to develop unsymmetrical biphenyls as novel anticancer agents.
- Wu, Gang,Guo, Huan-Fang,Gao, Kun,Liu, Yi-Nan,Bastow, Kenneth F.,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung,Xie, Lan
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scheme or table
p. 5272 - 5276
(2009/05/07)
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- Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB
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The synthesis of mono-, di- and trisubstituted gallic acids and their ester with similar or different groups including different acetal and ketals is described. Regioselective bromination on two ortho-positions of methyl gallate, which is very crucial for many organic syntheses, was achieved in high yield and purity. The α- and β-DDB were synthesized in high overall yield and purity from the regioselective bromoderivatives.
- Alam, Ashraful,Takaguchi, Yutaka,Ito, Hideyuki,Yoshida, Takashi,Tsuboi, Sadao
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p. 1909 - 1918
(2007/10/03)
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- Structural requirements for factor Xa inhibition by 3-oxybenzamides with neutral P1 substituents: Combining X-ray crystallography, 3D-QSAR, and tailored scoring functions
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The design, synthesis, and structure-activity relationship of 3-oxybenzamides as potent inhibitors of the coagulation protease factor Xa are described on the basis of X-ray structures, privileged structure motifs, and SAR information. A total of six X-ray structures of fXa/inhibitor complexes led us to identify the major protein-ligand interactions. The binding mode is characterized by a lipophilic dichlorophenyl substituent interacting with Tyr228 in the protease S1 pocket, while polar parts are accommodated in S4. This alignment in combination with docking allowed derivation of 3D-QSAR models and tailored scoring functions to rationalize biological affinity and provide guidelines for optimization. The resulting models showed good correlation coefficients and predictions of external test sets. Furthermore, they correspond to binding site topologies in terms of steric, electrostatic, and hydrophobic complementarity. Two approaches to derive tailored scoring functions combining binding site and ligand information led to predictive models with acceptable predictions of the external set. Good correlations to experimental affinities were obtained for both AFMoC (adaptation of fields for molecular comparison) and the novel TScore function. The SAR information from 3D-QSAR and tailored scoring functions agrees with all experimental data and provides guidelines and reasonable activity estimations for novel fXa inhibitors.
- Matter, Hans,Will, David W.,Nazaré, Marc,Schreuder, Herman,Laux, Volker,Wehner, Volkmar
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p. 3290 - 3312
(2007/10/03)
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- Synthesis of Garugamblin-2, a Macrocyclic Diarylheptanoid Constituent of Garuga gamblei
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The macrocyclic diarylheptanoid garugamblin-2 (1) and its constitutional and sterical isomers 17-19 were synthesized using the isoxazole derivative 8 for the introduction of the β-methoxyenone function.Ring closure was accomplished by an intramolecular Wittig reaction. - Key Words: Garugamblin-2 / Diarylheptanoids / Macrocycles / Garuga gamblei / Calculations, MMX, PM3
- Kaserue, Gyoergy M.,Nogradi, Mihaly,Kajtar-Peredy, Maria
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p. 361 - 364
(2007/10/02)
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- Biphenyl derivative useful in the treatment of liver diseases
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The present invention relates to a novel biphenyl derivative having a liver ailment-moderating action, which is effective for the remedy of liver diseases such as acute hepatitis and chronic hepatitis, a process for the preparation of this derivative and a liver ailment-moderating agent comprising this derivative as an active ingredient. Moreover, the present invention relates to a compound valuable as the intermediate compound for the synthesis of this derivative and a process for efficiently preparing this intermediate compound.
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